Walk north on Gulf Shore Boulevard from the Vedado Way beach access this month and the first thing you notice isn't a building. It's a fence line, a construction sign, and a rig working a bayfront lot that used to hold a four-story building with a pool deck and boat docks tucked behind it. The Executive Club stood on that site for more than fifty years. What's replacing it will stand twice as tall, and the reason why has less to do with a developer's appetite for height than with what it now takes to build safely on this particular stretch of water.
What Actually Stood Here
The Executive Club was a 46-unit, four-story cooperative built in 1969, restricted to residents 55 and older, with floor plans running 1,265 to 2,272 square feet and views across Outer Doctors Bay. It had a pool, boat docks residents could purchase when available, and beach access across the street. Hurricane Ian left it and several nearby buildings damaged badly enough that the Gulf Shore Association of Condominiums was fielding resident questions in late 2023 about which structures along this stretch were shuttered for good.
The site changed hands twice after that. Youngquist Brothers bought it for $60 million in 2023. Kolter Urban, a Delray Beach developer, bought it from them for $92.5 million in January 2025, a jump of roughly 54 percent in about two years for the same 3.07 acres. Demolition was already done by the time Kolter closed. What Kolter is building now is called 3300 Gulf Shore: two eight-story towers holding 51 residences, priced from $3.7 million, with a 16-slip marina.
The Math That Explains The Height
Here's the number that actually matters if you're trying to read this site correctly: 51 residences is barely more than the 46 units the Executive Club held. The unit count didn't balloon. The height did, and so did the size of each home, with floor plans now running 2,000 to more than 7,500 square feet compared to the old building's 1,265 to 2,272.
| Executive Club, 1969-2023 | 3300 Gulf Shore, 2026- | |
|---|---|---|
| Height | 4 stories | 8 stories, two towers |
| Residences | 46 | 51 |
| Unit sizes | 1,265 to 2,272 sq. ft. | 2,000 to 7,500+ sq. ft. |
| Foundation | n/a | Roughly 400 helical pilings |
| Status, August 2026 | Demolished 2023 | Foundation complete, vertical framing advancing; delivery targeted late 2027 |
That combination, roughly the same number of homes stacked twice as high in units built to a much larger scale, is a description of a lot getting rebuilt to the standard the site now requires rather than one getting redeveloped for maximum density. The Gulf Shore Association of Condominiums put it plainly in its own newsletter when construction began: the new buildings will be "the tallest buildings on the east side of Gulf Shore Blvd N in the Moorings." That's not a marketing line. It's a neighbor group noting, matter-of-factly, that this stretch of the bay side has never held anything this tall before.
What's Actually Underway Right Now
The first phase, once the seawall was raised to current code, was foundation work most residents wouldn't have noticed from the sidewalk. That gave way this spring to the roughly 400 helical pilings the project needs. Unlike a driven pile that's hammered into the seabed, a helical pile is turned into the ground much like an oversized screw, a method generally understood to run quieter than pile driving, which matters on a block currently hosting more than one active site at once.
As of the most recent construction update, from June 2026, the perimeter seawall was secured and BCBE Construction was driving the foundation pilings, with vertical concrete framing on track to advance through the remainder of the year ahead of a late-2027 delivery. Translated to what you're actually seeing on a walk this month: the towers are moving from foundation into structure, which means the height that's made this site notable should start clearing the fence line sometime before the year is out rather than staying hidden behind equipment much longer.
This Isn't A One-Site Story
The reason this stretch of Gulf Shore Boulevard feels perpetually under some kind of build right now is that it is. Residents of the Moorings and Coquina Sands started calling this 1.3-mile run of the boulevard, from the Naples Beach Club to Doctor's Pass, the Miracle Mile after Hurricane Ian, and the name stuck because so much of it was rebuilding at once. A resident-led committee, with Moorings Property Owners Association board member John Kneafsey among its members, has spent more than three years pressing the City of Naples on what happens to the public right of way itself: stormwater handling, whether utilities go underground, what gets planted, and how the sidewalks that residents cross with their grandchildren on the way to the beach get designed.
Along that same run of boulevard, three projects are moving on overlapping but distinct clocks:
- 3300 Gulf Shore, at the old Executive Club site, is in its foundation and early framing phase, with delivery targeted for late 2027.
- Olana Naples, Kolter's other project a few blocks north at 1121 Gulf Shore Boulevard North, is a far smaller undertaking, just 12 estate-sized residences.
- The Naples Beach Club redevelopment, further south toward the Miracle Mile's other end, has already reached closings on its Four Seasons-branded residences, meaning one project on this same corridor is essentially finished while another is barely above grade.
That spread matters if you're trying to figure out what a given fence line actually represents. Not every construction sign on this boulevard is at the same stage, and mistaking a foundation-phase site for a stalled one, or a nearly-finished one for a fresh start, is an easy way to misread how much longer any of this actually runs.
What To Watch For Next
If you're walking or biking this stretch through the rest of 2026, the practical marker to watch for at 3300 Gulf Shore is when framing starts to clear the top of the construction fence. Based on the current schedule, that's a late-2026 development, with the towers reaching their full eight stories sometime before the targeted delivery in the fourth quarter of 2027. Until then, the loudest part of the process, the piling work, is largely behind it. What's ahead is the slower, more visible climb of two towers that will be, by a neighbor association's own account, unlike anything this side of the street has held before. The old Executive Club, built in 1969 to a very different set of expectations for waterfront construction, is the version of this block that's disappearing. What comes next is the version built for whatever comes after Ian.
If you're weighing what a stretch like this means for a property you already own, or one you're watching from a distance, David W. Auston has spent two decades reading North Naples waterfront blocks exactly this closely. Explore My Properties to see what's currently available along Gulf Shore Boulevard and the rest of the Moorings.
